


Try Before You Buy

by SushiOwl



Category: Teen Wolf (TV)
Genre: 30 percent porn, 70 percent humor and weirdness, Anal Sex, Anatomy talk, Bottom Derek Hale, Derek is patient, Loss of Virginity, Lube talk, M/M, Stiles is a spaz, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2013-08-04
Updated: 2013-08-04
Packaged: 2017-12-22 08:47:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,804
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/911245
Author URL: https://archiveofourown.org/users/SushiOwl/pseuds/SushiOwl
Summary: <blockquote class="userstuff">
              <p>"Your penis scares the living hell outta me!" Stiles blurted out, and Derek's eyebrows went to go chat about the weather with his hairline.</p>
            </blockquote>





	Try Before You Buy

**Author's Note:**

> Beta read by [WhatTheHale](http://archiveofourown.org/users/whatthehale).
> 
> I **do not** give my consent to have my works listed on goodreads.

It wasn't that Stiles was scared, oh no, he was _fucking terrified._ Really his fear was mostly illogical, because honestly people had been taking it up the butt for, like, ever, but Stiles never had. And the more he obsessed about it, the worse it became. He had made the mistake of Googling the subject, and while most of the stories about first times were just fine, it was the few horror stories that stuck in his mind. There was one description of penetration that he kept going over and over in his mind like a mantra, from a guy with a penchant for especially creative adjectives, apparently it had felt like 'being split open by a set of steak knives and then being punched over and over in the gut.'

Stiles had needed to breathe into a bag after he read that.

He and Derek had been dating for months, and it was great, really it was. It was more than Stiles had ever thought his first relationship would be like. What was best of all was that he was taking his basics at the local community college and thus a for realsies adult, so his dad didn't start blowing up his phone with disappointed texts when he didn't come home at 9pm. He could stay out all night if he wanted! And he did want. He'd slept at Derek's loft almost as much as he slept at home. 

Now, he and Derek had done stuff, which was both awesome and awful. For one thing, making out with Derek as they ground their hips together was one of his new favorite pastimes. Right alongside it was when Derek jacked him off, using those amazingly broad hands and flexing, bulging muscles of his. And God, when Derek took them both in his hand and brought them to gasping, incoherent climaxes together, he wanted to die and prance through the pearly gates because he couldn't have accomplished anything more worthwhile in his life.

What was awful about this was that now Stiles knew what Derek's cock looked like. It was a beautiful cock, really, but _fuck_ was it intimidating. It wasn't any longer than Stiles's (and he had measured himself enough to know he was average), but it was thick. Like, _thick._ The more Stiles imagined it, the more he was positive it was like soda can thick. He knew it wasn't, but he was sure that was how it would feel. The thought made him clench in terror.

“I don't know why you're freaking out so much,” Lydia said as she devoted 30% of her attention to the conversation and the rest of the percentage to texting furiously with Jackson, Allison and Erica all at the same time. “Just use a liberal amount of lube.”

Stiles was glad for the amount of heeding he was getting at all. “How much is a liberal amount?” he asked as he anxiously picked at his curly fries. Even those weren't appetizing when his stomach was tying itself into a knot worthy of the Guinness World Records. “I mean, how do I know that it's not enough prior to the blinding pain? And how much is too much, y'know, the amount that'll make it sloppy and gross?”

Lydia looked up from her phone to give him a look that successfully communicated how hilariously hysterical he was being. “There is no amount that is too much,” she said, her brow twitching before she looked back down and started tapping away with her perfect thumb nails. “Well, I guess if he squirted the whole bottle inside you, that would be a bit much.”

“Oh God, I did _not_ need that mental image,” Stiles complained, covering his face with his hands and dreading the new nightmares he was going to have. “Lydia, what am I gonna do?” he asked for the millionth time during their lunch.

“You're going to calm the hell down for one,” she replied, and he looked up to find her glaring affectionately at him again. “If you spaz out during sex, of course it's going to hurt. It's all about muscle relaxation and trusting the guy you're boning. You trust Derek, don't you?” 

“Yeah,” Stiles said very quietly. It wasn't about that though. He wasn't sure he'd be able to get out of his own damn head long enough to enjoy what was going on. No matter how talented Derek's tongue was (and God was it ever), he was going to be constantly thinking about the giant fucking thing that was supposed to go _inside him._

“Then stop being a total freak and just enjoy yourself, God,” she said with a huff. “It's not like you're a pioneer in anal sex, Stiles. Derek will probably be able to guide you through it. Haven't you done any research on your own?”

“Of course I have,” Stiles said, shuddering because he didn't want to recount the terrors he'd discovered. Lydia didn't need to know that he'd draped his blanket over and around himself and held his pillow in a death grip as he read personal testimonies. He shifted and watched her for a moment as she typed out a no doubt grammatically perfect veiled threat to her boyfriend. He did not envy Jackson during a couple's quarrel with Lydia. 

He swallowed. “Have you tried it?” he asked quietly.

He wasn't even sure she heard him because she finished her text before setting her phone down and looked at him. “Anal?” she asked, taking her cup and sipping through the straw. He nodded. She just made a noise like 'pssh' and waved a hand dismissively at him. “Of course I have.”

“Do you like it?” he asked, leaning forward to peer at her owlishly.

She just shrugged and picked up her phone as it buzzed, either with a waning complaint or withering concession from Jackson. “It's okay. You have an advantage over me in the act though.”

He stared at her, waiting for her to elaborate, and she just gave him a long look of annoyance, before her brow went up. He jerked back as she realized what she meant. “Oh! That.” He had no idea how prostate stimulation felt, and he must have made it totally obvious because she sighed at him.

“Have you done any experimenting on your own?” she asked, and he shook his head. “Oh my God, you moron. Buy some lube and do that.” She shook her head at his general hopelessness. 

He swallowed, nodding. He'd do that. He would!

###### 

Stiles was honestly going to do that. Really. He had actually bought the lube too! Though he had needed to do some serious research about it, because research was his thing. It made him feel prepared and safe. (Sometimes.) He found out that KY Jelly was shit because it had this stuff called glycerine in it and apparently a whole slew of things that would irritate sensitive skin and maybe cause yeast infections. 

Could butts get yeast infections? He would Google that later.

Anyway, he never got around to playing with—fingering—himself. He had wanted to, but he kept looking at the bottle of lube in his drawer, getting tunnel vision as he thought of all implications that came with it. He needed to experiment on himself to get used to the sensation of being stretched. He needed to do that so he would be able to take Derek's giant cock, shit! No! Abort abort abort! He ended up under his covers curled into a ball every time he thought about it.

That meant he wasn't prepared in the slightest when _the time_ came.

He had a four day weekend break from school, and he was supposed to spend it at Derek's being all couple-y and sexual and stuff. They'd come to an agreement, mostly in vague terms, that this weekend would be the weekend they did the deed. And while Stiles had been ecstatic about the prospect of punching his V-Card with Derek in the beginning of their relationship, now the idea nearly sent him into an anxiety attack.

Worst of all, Derek didn't know that anything was wrong. When he had asked him 'Are we still on for this weekend?' over the phone, putting a kind of sultry emphasis into the word 'on', Stiles had squeaked out an affirmative. Yeah, he was peachy. He was ready and raring to go! They were so on for this weekend that they'd never been more on for anything else ever. Derek had taken his panicked rambling as excitement and told him that it would be a weekend they'd never forget. 

Maybe Stiles should just take his hyperventilation bag with him.

As he drove to Derek's loft, he blasted music in his jeep in the hopes of drowning out his thoughts. But then the walk up to the door was drastically quiet in contrast. His thoughts were running rampant in the quiet, and he honestly felt like he was making the long walk to the gallows. And that was totally unfair to Derek, though now he was imagining him in a tight leather executioner's outfit, which gave him conflicting emotions.

Derek answered the door looking about as hot as he ever did in sweats and a black tank top with his feet bare. The easy smile Derek always gave him in greeting made Stiles's insides all gooey and warm. God, he wanted so badly to have hot and heavy sex with this man. Multiple times over the next four days. In every single position.

"Hey," Derek said, stepping to the side to let Stiles in.

Stiles immediately pulled off his backpack and unzipped it, showing him the contents. "I came prepared," he announced as he stubbornly tried to ignore the trembling of his fingers. Inside his bag was his unopened bottle of lube and an industrial sized boxed of XXL condoms.

Derek stared into the bag for a long, silent moment before his eyebrows crept up toward his hairline and he lifted his eyes to Stiles's face. "I was thinking pizza and Netflix first, but if you want—"

"Pizza is good!" Stiles all but shouted in interruption. One of Derek's brows came down while the other stayed quirked inquiringly. Stiles coughed against his hand as he swung his backpack back and forth by his side. "Netflix is good too." Anything and everything to delay the inevitable.

Derek blinked at him only once. "Right," he said, before he took Stiles's backpack from him them moved toward his couch and entertainment center. "Meat lovers okay?" he asked as he picked up his phone off the coffee table. Stiles just nodded mutely, and Derek stared at him. "Are you going to come in, or?"

Stiles burst into movement, propelling himself gracelessly and ending up on the couch. He sat with his spine straight as an arrow and his hands on his knees, his legs tightly together. He must have looked as wound up as he felt, because Derek continued to gaze at him instead of ordering their pizza.

Finally Derek set the backpack and the phone on the coffee table and sat next to Stiles. "You okay?" he asked, nudging Stiles thigh with his knee.

"Yeah," Stiles replied, and his voice shook so he knew Derek would see right through his lie.

"What's wrong?" Derek asked in his 'you're being strange and I don't like it' voice. When Stiles just swallowed and didn't answer, he moved closer, pressing against his side and putting his arm around him. Stiles immediately melted and leaned into him, curling his fingers in the hem of his shirt. "You're nervous, aren't you?"

"A bit." Understatement of the fucking century.

"Don't be," Derek told him as he nuzzled the top of his head. "It's no big deal."

Oh no, it was a big deal, a huge deal, a gargantuan deal! Stiles huffed out a breath before making some kind of pathetic noise that made Derek's other arm come around him and give him a squeeze.

"Come on," Derek said as he rubbed his back. "Once you've eaten and had time to relax, you'll be fine." He drew back enough to take Stiles's chin with his finger and tilt his head up for a kiss. 

Stiles made a tiny sound as warmth bloomed down his spine. No matter how worried he was, Derek's kisses always made him feel cared for and at ease. It was when they drew apart and all his anxious thoughts rushed back that was the problem.

Derek kissed the bridge of his nose. "We can watch Doctor Who or something, whatever you want."

Honestly Stiles would rather face a dalek or a weeping angel right then, because he was sure that Derek's dick wouldn't be deterred by a sonic screwdriver.

The pizza arrived partway through the first episode they were watching, and they chowed down silently as the Doctor, the Ponds and River Song barreled through an adventure. Stiles was leaning into Derek, one of his legs draped over his thigh. Derek kept touching him lightly, running his knuckles along his arm or toying the the hairs on the back of his neck. After the next episode, Derek didn't queue up another, and Stiles knew he was in trouble.

Derek turned so he could brush his lips along Stiles's neck. "Do you want to watch another episode?" he asked in a low tone that always made Stiles's cock twitch in interest.

"Kinda," Stiles breathed out before he sucked in a breath when Derek ran his teeth along his earlobe.

"Or do you want to do something else?" Derek murmured, and Stiles could just hear the smile in his voice, causing gooseflesh to raise on his arms.

Stiles wanted a lot of things. They could watch more Doctor Who. They could watch something else too. Stiles had been trying to get Derek into Babylon 5, and now was the perfect time for new experiences.

“I think we should take this to bed,” Derek said, before he latched his his mouth over the spot where Stiles's neck met his shoulder, sucking hard.

Stiles gave a strangled kind of noise. When he was thinking new experiences, he didn't mean the ones that have to do with his butt.

Derek continued to draw Stiles's blood to the surface, and Stiles was busy trying not to turn into a puddle. When Derek pulled back, he licked the spot, and Stiles was sure he'd have a nice hickey to take back to college with him. Derek lifted his head to look Stiles right in the eyes, and crap, now that they were looking at each other Stiles couldn't drop his eyes evasively. 

Then Derek asked the question that turned Stiles's spine to ice. “Do you still want to?”

No. “Yes.” Goddammit, mouth. 

Derek smiled that soft, quiet little thing he reserved only for Stiles, before he stood up, picking up the backpack then offering Stiles his other hand. Stiles glanced around for an excuse, briefly thought about complaining that there was still a piece of pizza left so Derek better get on that, but in the end he took his hand and stood up. Derek pulled him up the spiral staircase to the area with the bed and accompanying furniture.

Stiles felt like the first time he had been up here with the goal of taking off at least some of his clothes and rolling around with Derek. He had been apprehensive then too, but in the months since then he'd become bolder, so much so that he could initiate things with a pounce. But now he felt like he'd backpedaled nearly a year.

He numbly allowed Derek to pull him over to the bed, where he toed off his shoes before crawling to the middle of it and resting back on his heels. Derek followed him, sitting down and bracketing Stiles with his long legs. He dug into the bag, pulling out the lube and turning it over in his hand.

"Yes?" he asked, furrowing his brows at the brand name. "As opposed to 'No?' Why do I have a feeling this was expensive? What's wrong with KY?" He glanced over to his bedside table where his KY was stored.

"KY is so cheap because it uses crap ingredients," Stiles blurted out, glad to be on this topic because his research prepared him for it. "It has glycerine in it, which can irritate the skin. You know how sensitive my regular skin is. God knows about down—down there. It can cause yeast infections!"

"Guys can get yeast infections?" Derek asked in a stunned voice.

"I have no idea, but better safe than sorry, right? Also KY has these things called parabens. They're some kind of, I don't know—" He made a vague, wild gesture. "Estrogen doppelganger! They're found in breast tumors, and prolonged exposure can lower your immune system." Derek stared at him with wide eyes, and he wilted. "I guess you wouldn't have to worry about that as a werewolf, would you?"

In response to that, Derek leaned over, dug his KY out of his drawer and promptly dropped it in the trash bin. Stiles felt strangely proud about that, because he'd always thought of Derek as a guy that was very set in his ways. Derek dug out the condoms box, his brow twitching up for a second before he set both it and the lube near the pillows before he let the backpack fall off the edge of the bed.

Stiles made a tiny noise as Derek urged him into his lap, catching his lips with his own and sucking on the bottom one. Stiles opened his mouth immediately when Derek went questing with his tongue, moaning softly at the taste of spicy sausage and something that was all Derek. Stiles wanted to say that he tasted like fresh rain on spring flowers or maybe the way damp, warm earth smells, but those were contradicting tastes and he didn't even know anymore. 

What he did know is that he could never, ever get enough of kissing Derek. He tangled his hands in his hair and surged up against him, lifting a bit onto his knees. Derek rumbled out a growl in response, and shit the goosebumps were back, raising the hairs on his arms and legs. He could get lost in this man, forget all sense of time and spacial awareness until everything was Derek and his tongue, his heated skin and his glorious hands.

Stiles let Derek break the kiss long enough for those hands to lift Stiles's shirts over his head. Then he moaned and dropped his head back as Derek's tongue started a hot, wet trail down his neck to his chest. He gasped when that tongue located one of his nipples, lavishing it until it stood hard and at attention. He scraped his teeth lightly across it, making Stiles shiver, before he moved to the other nipple and gave it the same VIP treatment.

Derek turned toward the pillows and laid Stiles down, shifting onto his hands and knees to press a burning path of kisses down his sternum to his belly. Stiles let out a shocked, high pitched note when Derek playfully plundered his navel with his tongue, smiling as he did so. Asshole. But damn if that didn't have Stiles writhing and panting. His dick was pressing hard against his undies and pants zipper, straining the fabric.

"Derek," Stiles pleaded, and the man took pity on him, sitting up and pulling off his shirt to reveal his gosh darn beautiful chest. Stiles had to attack it, lunging for him and wrapping his arms around his broad chest. He splayed a hand over the triskele tattoo as his lips found a nipple, and he sucked, reveling in the low, quick breaths it drew from Derek.

Privately, he wondered if he could make Derek scream his name.

Derek didn't let him get much further, pushing him back down and undoing his jeans to reveal his Superman briefs. He stopped, looked at Stiles's face, looked at the briefs then back at his face with an eyebrow arched like 'Really?'

Stiles just grinned at him. "What? No jokes about my little Man of Steel?"

Derek rolled his eyes like he was regretting many a life choice, before he tore Stiles's pants and underwear with enough force to nearly rip the fabric to bits. He tossed the offending articles of clothing behind him, and Stiles nearly complained when he watched them fly over the floor guardrail and down into the living room, but then Derek was pushing his thighs apart. 

Stiles was sure the sound he made was squeaky and embarrassing when Derek leaned in and dragged his tongue along his hip bone and down the skin wrinkle where his thigh met his pelvis. He knew the sound he made when Derek nipped and laved his inner thigh was a tragic, keen-like thing, but he was beyond caring now. Derek didn't seem to mind the chorus of sad, virginal noises he made anyway.

Derek breathed a hot, teasing breath along Stiles's aching cock, causing him to try to buck up into the feeling, but Derek held him down. He flicked the tip of his tongue along his balls, which was a torturous mixture of tickling and pleasure that made him moan and writhe. The last time that Derek had used his tongue in the vicinity, the whole endeavor had been over far too quick. He would never forget the sound of Derek _swallowing_ him down though.

But Derek wasn't looking for a repeat performance. He leaned back up and shifted so he could shimmy out of his sweats—no boxers, what a naughty Sourwolf—and kick them away, before he moved to loom over him in all his glorious nudity. Stiles spotted Derek's cock all hard and ready to go before Derek kissed him again, his hand pawing around beside them until it closed around the lube. Then he sat back between Stiles's open legs, popping the cap.

The sound was like an explosion in his brain, and all those unwanted thoughts came rushing back. "Oh God, stop!" Stiles cried far more loudly and desperately than he had meant to, holding his hands out defensively. Derek halted with the lip of the lube against his fingers, eyes blowing wide in surprise. "Shit, sorry," Stiles whined, before he rubbed at his eyes frantically. "Sorry," he said again, the word much smaller and infinitely more ashamed.

"Stiles?" Derek asked quietly, closing the lube again and dropping it onto the bed. "What's the matter?" He leaned over Stiles, his hands on either side of his chest.

"Your penis scares the living hell outta me!" Stiles blurted out, and Derek's eyebrows went to go chat about the weather with his hairline.

"Excuse me?"

"It's massive! I mean, look at that thing!" He pointed, and Derek did as instructed. "How is it even supposed to fit?"

Derek looked at him incredulously. "It's not that big," he tried, looking like he never expected to have this conversation in his life. Most men aren't faced with the contradictory statement that a big penis is a bad thing.

"Is too. It's huge! Like, scary huge. And I have no idea what to expect from it." Derek wrinkled his brow at him like he'd just accused his dick of possibly being a venomous serpent. And Stiles gulped because he was about to reveal just how deep his paranoia went. "Like—like do you have a knot?"

"A what?" Derek asked, looking more and more lost by the second.

" A knot! Y'know, bulbous glandis! A bulge at the base of your penis. Wolves, coyotes, dogs and shit have them. It'd be like tennis ball!" He was breathing hard, very caught up in his conspiracy theory.

Derek blinked several times rapidly. "I don't have that."

Stiles was relieved, but only for a split second. “Does your wolf form?”

“I haven't checked,” Derek said slowly.

Stiles gulped in a breath. “Maybe you should, because what if you wolf out accidentally? I don't think I'm even capable of—“

“Stiles, Stiles, calm down,” Derek said quickly, leaning over him further and taking his face in his hands. “Breathe. Your heart is racing.” He leaned his forehead against Stiles's, breathing in an obvious, slow way, and Stiles stared up at him, wide-eyed, as he tried to match it. 

Eventually he succeeded, and he felt the tension leave his body one part at a time. It started with his toes. They uncurled, and his ankles relaxed from their extended position, the soothing moving up his calves, which stopped flexing. His hips relaxed from being pressed firmly into the mattress, his ass unclenching in the process. He thought he felt his back loosen vertebra by vertebra, but that was probably impossible and just his overactive imagination. His shoulders eased, and his jaw ached when he stopped pressing his teeth so firmly together. Finally, he released the white knuckle grip on the covers.

“There,” Derek said softly, drawing back so Stiles wouldn't have to cross his eyes to look at him. “Now can you tell me why you're upset in a less crazy way?” Usually those words or ones like them were filled with annoyance, accusation, and/or rage, but Derek's voice was calm, his eyes the gentle pale green with the earthy brown rings around the pupils they always were. If Derek were impatient, they'd be red.

Stiles swallowed and felt his chin wobble. “I'm afraid it's going to hurt.”

Derek tilted his head as his eyebrows bowed sympathetically. He sat back and pulled Stiles up into his arm so he could hold him him flush against his chest. Stiles wrapped around him like an octopus, breathing him in and trying to remain calm. “It doesn't have to hurt,” Derek said softly against his ear, and Stiles whined. 

“I tried to research it,” Stiles whimpered pathetically, crossing his arms around Derek's neck. “I found useful information about breathing and relaxation, and then I found the horror stories. And that's all I can think about! I mean this one guy, he—he tore and had to go to the emergency room. He said he's never seen so much blood. I'm not good with blood. I'm not.”

Derek heaved a sigh before he gave a laugh, a deep rumble in his chest that warmed Stiles to the core. “I need to put a parental lock on your internet privileges,” he grunted as he ran his hand up and down Stiles's back soothingly. “That's not going to happen. I would never let it.”

Stiles clung to him a little more, shaking his head. “You can't control everything, Derek.” No matter how he may try, there was no way that Derek could predict every outcome and protect against the unpleasant ones. Stiles had never been one to let fear cripple him before, but this was different. Not only did he not was to end up in agony, he wanted their first time to be just right. He wanted butterflies and rainbows and confetti.

Derek held him for a little while longer, before he pulled back enough to look at his face. “Look, Stiles, if you're so afraid of doing it, we don't have to.” There was a look on his face kind of like resignation. Stiles didn't like seeing his wolfy boyfriend so defeated.

“No, that—“

“You can do me instead,” Derek said, totally straight faced and serious.

Stiles stared at him for a long moment, before he stuck his pinky finger in his ear and wiggled it around a little bit. He couldn't have heard that right. He was experiencing panic induced hallucinations. “Say what now?” he asked.

Derek huffed, before he leaned in and brushed his lips along Stiles's. “I said,” he growled out, and it wasn't his threatening growl, it was his 'I'm going to do unspeakable things to you' growl. “You should fuck me.” Maybe it was actually his 'I'm going to let _you_ to unspeakable things to me' growl. That was new.

Stiles hadn't known this was an option! He swallowed hard and gnawed his lip for a moment. “Are you sure?” he asked, feeling a bit silly asking that of a man who had untold amounts of sexual experience. Well, maybe not untold. Note to self: badger boyfriend about sexual history.

Derek just smiled at him, putting their foreheads together. “I'm sure. I want to be with you, Stiles. I don't care how.”

Stiles didn't know he was still capable of blushing. After furious make out sessions, hand jobs and frotting (yes, he'd looked up the name of it), he'd thought that his skin was no longer able to go so embarrassingly pink. He was wrong. He wanted to hide his face and sink into the floor. Along with flushing down to his toes, it felt like butterflies were swarming inside him, so light and fluttering that he was about to take off into the sky. Wordlessly, he nodded.

“After you watch me, you'll see it's not so bad,” Derek assured him.

Stiles wasn't so sure about that, but he was willing to give it a shot. He squared his shoulders and straightened up. “Okay, so what do I—“

“You're not going to do a thing,” Derek said immediately, cutting him off before he turned and pushed him off. “Not yet. You're going to watch before you can't be trusted to do anything without spazzing out.” 

Stiles wanted to defend his honor but he ran out of steam before he got any words out. “That's not entirely untrue.”

Derek grunted with a smirk, shifting so he was nestled back against the pillows. He lifted his knees and let them fall apart, and _oh_ , that was an angle Stiles had never seen of Derek before. Honestly he'd never even thought that Derek would—would bottom, but there he was spreading lube on his fingers. If this was a dream, if Derek had knocked him out to keep him from having a full blown anxiety attack, Stiles was not ready to wake up yet.

Derek used his free hand to gather up his heavy ball sac and move it out of the way, running a lubed finger down his perineum before circling it around his hole. Stiles leaned in, entranced, and he flushed when Derek chuckled, looking up to find him smiling like the dick he was. "Keep watching," Derek said, his voice laden with all things sultry. Stiles did as told, sucking in a breath when Derek breached himself and that finger disappeared up until the second knuckle.

The sigh that drifted past Derek's lips made shivers roll up and down his spine. He watched Derek's finger move in and out of him, feeling his erection from before come back with a vengeance. God, this was hot. It was, like, uber hot. The supreme hotness. There wasn't a thing he'd witnessed in his life that was hotter than Derek fingering himself.

That was until Derek pressed another finger in and made this _noise_.

Stiles sat back, taking in the whole picture rather than zeroing in on one detail. Derek was moving, undulating his hips to meet his fingers. He was slowly, languidly stroking his cock with his other hand, thumb playing over the slit with every upstroke. He spread his fingers apart, before he hooked the rim of his hole and _pulled_. Stiles had to wonder if that hurt, but the sound that Derek made was definitely not a pained one.

Stiles also had to wonder why he was taking his time, despite the sheer sexiness of it. When he looked at Derek's face, he understood. Those half-lidded eyes and that faint smile playing along his lips as Derek gazed up at him, looking just about as appealing as anything in the whole damn world. The bastard was putting on a show. When Stiles let out a surprised whine, Derek smiled wider before he lifted his leg to set his foot on the mattress and finger himself harder, his hips pumping.

Stiles was going to need some serious rewiring after this, because it was frying his brain.

Derek fisted his cock faster, his mouth falling open to let out these little grunts and moans that Stiles wanted to swallow, but he didn't dare move because he wanted to watch this forever. It made him wonder if Derek did this when he was alone. He bit his lip as he wondered who Derek thought about when he did this. He very selfishly (but who cares because Derek was his) mused if Derek thought about him. Did Derek fantasize about Stiles fucking him?

Abruptly Derek groaned loudly, his hand squeezing the base of his cock as his fingers stilled deep inside of him. Stiles watched him, taking in his thrown back head, the bared neck and the trembling of his muscles. Oh fuck, did Derek just nearly come on his own fingers? 

Stiles's brain did the mental equivalent of a key-smash.

“Jesus,” Stiles whispered as Derek tried to regain control of his breathing. Derek chuckled at him before he reached over, grabbed Stiles by the wrist and pulled him closer. Derek snatched the back of his head and pulled him in for a slow, deep kiss that ended in Stiles moaning hard as Derek sucked on his tongue. 

Derek's hand was searching next to him, and Stiles peeked at it out of the corner of his eye as Derek was taking inventory of his teeth. When Derek's hand landed on the box of XXL condoms, Stiles groaned and pulled back enough to gasp out, “I think those are too big for me.” His cheek burned as he said it, and yup, still capable of blushing.

Derek looked at the box, before he grunted then reached over and pillaged around in his bedside drawer. “Too big for me too,” he muttered, and Stiles was pretty sure Derek was close to communicating in just growls and teeth baring.

“Are not,” Stiles said immediately, because honestly, had Derek even compared his cock to normal ones?

“Are too,” Derek replied, his lips quirking up, before he brought the condom up and ripped it up with his teeth.

Stiles stared as his brain just checked out entirely. All he was able to do was watch as Derek lifted up and rolled the condom down on Stiles's dick, giving him a squeeze before he slicked him up further with a dollop of lube. He let out a rush of air as Derek grabbed him by taking handfuls of his ass, pulling him closer, and Stiles's hands scrambled before landing on Derek's thighs.

“Wait,” Stiles said, Derek looked up at him with an expression that said he was quite tired of waiting, thank you. Stiles licked his lips. “Shouldn't we put a pillow or two underneath you?” When Derek stared at him, before sucked in a breath. “I read online that it helps with the—the, y'know, angle of penetration.”

“So your internet research actually did some good after all,” Derek said as he snatched his pillows and stuffed them under his hips, and now Stiles could definitely see _everything_.

“Some of it,” Stiles said as he stared, not even bothering to hide how entranced he was by this whole situation.

Derek grabbed his ass again, pulling him forward, and he stumbled on his knee, head of his cock sliding against the slickness of in the cleft of Derek's ass. That was a wholly new sensation he wasn't prepared for, and he keened. “Stiles, I swear to God,” Derek growled at him, eyes shimmering with red for half a second.

“Sorry, sorry!” Stiles said as he took himself in hand and lined up. He looked at Derek's face again, glad that there was only cool green gazing back up at him.

Stiles would have liked to wax poetic about the way it felt to press inside of Derek, but that would have required for his brain to be able to think of anything beyond 'hot' and 'tight.' He stalled, full seated inside Derek, trembling and already panting hard. He was holding Derek's hips hard, his fingers digging in. He was also pretty sure that he was ascending to a plain of existence that was only pleasure.

“If you don't start moving,” Derek growled at him, making him focus. “I'm going to flip you over and ride you.”

That was a punishment?

Stiles was sure he'd last all of 0.5 seconds if Derek did that, so he drew back a bit and thrust back in. Derek made a noise like 'uhn' and Stiles made a noise like 'ohGodfuck.' It took him awhile because he was barely coordinated when firing on all cylinders and far from it right now, but Stiles managed to get a rhythm going. He didn't know if it was fast or hard enough, but Derek didn't complain. It was certainly enough to make Stiles's eyes roll back in his head.

Derek wrapped his legs around Stiles's waist, locking his ankles over his butt. Having those meaty thighs gripping him drove his pleasure to new heights. He let out a chorus of groans, grunts and pants, punctuating each time his hips smacked against Derek's ass. He may have been loud, but he wasn't the only one. Derek met his sounds with ones of his own and he rocked his body to meet him.

“Stiles, Stiles,” Derek called out breathlessly, tossing his head back and breathing hard through his open mouth. 

Stiles could have cheered. He was doing it right! He was the sex master!

Derek grabbed his arms to jerk him down into a harsh kiss that involved a lot of crushing lips and some teeth. Stiles moaned at their tongues danced, and he wasn't sure how he kept up his rhythm, but he did, and Derek was there thrust for thrust. Derek's hands moved down his back, nails scratching lightly, before they reached his ass and squeezed, urging him to go faster.

Stiles did, his kissing becoming increasingly sloppy as ecstasy flourished through his body. When he came, it was with a strangled cry, lightning flashing behind his eyelids as he slammed inside of Derek as deep as he could get. He wanted to collapse immediately after, but he held himself up on his trembling elbows and panted, opening his eyes to look at Derek.

There was a hardness pressing into his stomach, and he flushed when he realized what it was. He lifted up onto one hand to look down at Derek's thick cock still at attention. “Oh,” he said, looking back at Derek's face. “You didn't—should I—“

Derek grabbed him by his hair and jerked him back down. “Shut up,” he growled at him, before he shoved their mouths back together. Derek's other hand moved between them, taking himself in hand and starting to stroke in earnest. Stiles could feel his knuckles run along his stomach as Derek moved his hand, and there was something weirdly hot about that.

Derek arched back with a cry, heat painting their stomachs and his ass muscles clenching around Stiles's softened cock in a way that made his eyes cross. Then he sagged, arms coming around Stiles to pull him down and snuffle against his neck. He was always so cuddly after coming, and it was so cute. Stiles sighed against him, nudging his nose against his ear before he kissed it.

Shifting back a little, Derek, pushed his shoulder a little. “Sit up a bit,” he grumbled, all sated and sleepy now. Stiles did as told, and Derek slowly removed the condom, before he tied it off and dumped it into the trash. Then he wrapped his arms around him again and pulled him close.

“We're all sticky,” Stiles sighed into his ear.

“Don't care,” Derek replied, before he tilted his chin up a little. “Less scared now?”

Stiles blinked, before he realized that, yeah, he was less scared. Derek's cock was still intimidating, but now he was thinking that if they used plenty of lube and were liberal with the stretching beforehand, he'd be just fine. He nodded wordlessly into Derek's neck, and Derek chuckled before giving him a squeeze.

###### 

The next night, Derek prepared him slowly, attentively. His slick fingers eased the tension out of his hole masterfully. He ended up using three fingers after Stiles kept insisting that Derek was so huge. Stiles didn't know how to explain it, but the feeling of Derek's fingers stretching him was a kind of fulfillment he had never known he needed. Though nothing could compare to the explosion of pleasure of Derek's cock inside him.

Oh, and Stiles's prostate was his new best friend.

**Author's Note:**

> All the cookies and love to [WhatTheHale](http://archiveofourown.org/users/whatthehale) for the super fast beta read! I have no idea where I'd be without her, because she translates my crazy into a language readable by normal people.
> 
> I poked a little fun at knotting kink in this story because I just had to, even though I love it and write it myself. My other Stiles/Derek story is all omegaverse. 
> 
> Anyway I hoped you enjoyed this! I haven't read enough bottom!Derek, so I thought I'd make a bit of my own.


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